Why Cross-Selling Fails and How to Avoid Failure?
Cross-selling is a great way to boost company growth. Unfortunately, many cross-selling initiatives fail. We address a few common issues that cause cross-selling to fall flat and offer advice on mastering cross-selling.
“We’ve acquired a new company because we believe their product fits well with our customer base—and vice versa.”
This is often heard in the tech world, where cross-selling initiatives are launched following acquisitions, new product developments, or strategic partnerships. But while many embark on these initiatives with high hopes, only a fraction truly succeed.
Regardless of the reasons behind a cross-selling push, the big picture and main challenges are usually similar.
Why Cross-Selling Fails?
Cross-selling initiatives can stumble for a variety of reasons. Here are the top three pitfalls:
- Insufficient planning and unrealistic expectations
- Misaligned go-to-market strategy
- Lack of cross-selling training and culture
Let’s explore these factors and how they can be addressed to avoid failure.
Unrealistic Expectations Without Proper Plan for Cross-Selling
Successful cross-selling requires more than enthusiasm—it demands a well-structured plan that accounts for the customer journey, buyer personas, and, most importantly, pain points to solve. Launching a cross-sell campaign without a proper plan means not identifying the right timing to introduce a complementary product, missing out on crafting a relevant message, or barely segmenting any customers. When these essential elements are absent, cross-selling efforts can feel disjointed, random, or even intrusive, eroding customer trust.
“Here’s the new product. We want you to push it now to all customers.”
Unrealistic expectations compound cross-selling issues. Many companies expect rapid revenue growth or won opportunities without considering the complexities above. Disappointing results can result in additional stress and frustration. When companies skip the time needed for proper customer education or fail to demonstrate value, cross-selling efforts often falter, leading to abandoned strategies that might have thrived with patience and realistic goals.
How to avoid this: Simply put—create a comprehensive plan. Planning is essential for success here. A robust cross-selling strategy includes more than just one product training and a pitch deck. The depth of planning will depend on how closely the new product relates to the existing one. You can plan lighter and move faster if the latest offering serves the same buyer and complements the original's purpose (like a sales analytics tool for CRM customers). But, if it’s solving a different problem for a new buyer segment (such as adding customer support software to a CRM), a thorough plan is crucial, and more time is required to play it out.
Unsuitable GMT Strategy For the New Product Portfolio
Another common pitfall is relying on an existing GTM strategy for a new product. Many companies assume their established sales approach will also seamlessly carry the new product. However, a GTM strategy is typically tailored to the target market, buyer personas, and value proposition of the original product, and it may not align with the realities of the new offering.
“Let’s offer discounts!”
The misalignment between the product and GTM strategy can lead to customer confusion or a sales team struggling to convey the new product’s benefits effectively. When the messaging and branding feel off, sales cycles drag, win rates drop, and sometimes discounts are rolled out to move the product, ultimately reducing potential revenue.
How to avoid this: Either adjust the GTM strategy to support multiple products or create a dedicated approach for each. Developing tailored sales enablement materials and adjusted messaging to highlight product synergies can make all the difference. Aligning the sales process across a multi-product portfolio ensures each product is positioned effectively, allowing the sales team to identify cross-sell opportunities. Start from discovery and work your way through the sales process.
Unfamiliarity with Cross-Selling
A lack of cross-selling culture and training often leads to missed opportunities, as teams focus solely on selling the original product without exploring broader needs within the customer’s organisation. For cross-selling, teams must engage customers beyond the initial sale. To enable this, leadership must foster a culture of curiosity and discovery. This means asking questions that reveal broader customer goals, challenges, and needs.
"Always be closing!"
Without a curiosity-driven approach, cross-selling efforts can feel shallow. Lack of curiosity leads to not learning customers' proper needs, and cross-selling initiatives will likely fail before they even begin. Not curious sellers will conduct discovery badly and, for example, fail early by speaking with the wrong contacts (existing contacts at the customer organisation might not be relevant to the new product).
How to avoid this: Prioritise discovery and cultivate curiosity within your sales team. Encourage them to look beyond the initial product to understand customer goals across departments. Their training should focus on probing questions and uncovering broader needs, coupled with a firm grasp of the complementary products. Highlighting internal success stories can also reinforce the value of cross-selling by showing real-world impact on customers. Effective cross-selling hinges on training that enables sales teams to conduct holistic discovery conversations, uncovering needs across the organisation and positioning themselves as trusted advisors rather than just product pushers.
Making Cross-Selling a Key Part of 2025’s Sales Results
To maximise the impact of cross-selling in 2025, focus on systematic planning, aligning GTM strategies across products, and embedding a culture of curiosity in your sales team. You can use our Sales Plan Template to develop a plan that includes cross-selling initiatives. Cross-selling can deepen customer relationships and fuel growth, setting the stage for a successful year.
